(2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione

Base Information

• Chemical Name: (2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione
• CAS No.: 1337551-93-5
• Molecular Formula: C₂₄H₁₈N₂O₅
• Molecular Weight: 414.417
• Mol file: 1337551-93-5.mol

Synonyms:(2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione

Chemical Property of (2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione

There total 3 articles about (2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

3-(4-nitrophenyl)-2-propenal (1734-79-8) + 1-benzylisatin (1217-89-6) → (2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione (1337551-93-5) + 1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione

Guidance literature:

With (S)-5-{bis[3,5-bis(trifluoromethyl)phenyl](hydroxy)methyl}-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c]-1,2,4-triazol-2-ium tetrafluoroborate; caesium carbonate; In toluene; at 20 ℃; for 12h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c1cc13860j

Reference yield:

1-benzylisatin (1217-89-6) + 3-(4-nitrophenyl)propionic acid (16642-79-8) → (2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione (1337551-93-5) + 1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione

Guidance literature:

With (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate; HATU; In 1,2-dimethoxyethane; at 20 ℃; for 12h; Overall yield = 80 %; enantioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201500345

Reference yield:

3-(4-nitrophenyl)-2-propenal (1734-79-8) + 1-benzyl-3-hydroxyindolin-2-one (92552-73-3) → (2R,3S)-1'-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione (1337551-93-5) + (2S,3R)-1′-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3′-indoline]-2′,5(4H)-dione + 1′-benzyl-3-(4-nitrophenyl)-3H-spiro[furan-2,3′-indoline]-2′,5(4H)-dione

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; nitrobenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃; Overall yield = 78 %; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1039/c6sc04135c

upstream raw materials:

3-(4-nitrophenyl)-2-propenal

1-benzylisatin

3-(4-nitrophenyl)propionic acid

1-benzyl-3-hydroxyindolin-2-one